| Identification | Back Directory | [Name]
5-Bromo-1-methyl-2-oxoindoline | [CAS]
20870-90-0 | [Synonyms]
5-bromo-1-methyl-oxindole
5-broMo-1-Methylindolin-2-one
5-bromo-1-methyl-2-indolinone
5-Bromo-1-methyl-2-oxoindoline
5-Bromo-1-methyl-2-oxindole97%
5-bromo-1-methyl-3H-indol-2-one
5-Bromo-1-methyl-2-oxindole 97%
5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one
2H-Indol-2-one, 5-broMo-1,3-dihydro-1-Methyl-
5-Bromo-1-methylindolin-2-one, 5-Bromo-1,3-dihydro-1-methyl-2H-indol-2-one | [Molecular Formula]
C9H8BrNO | [MDL Number]
MFCD00464061 | [MOL File]
20870-90-0.mol | [Molecular Weight]
226.07 |
| Chemical Properties | Back Directory | [Melting point ]
132 °C | [Boiling point ]
418.1±45.0 °C(Predicted) | [density ]
1.589±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
-0.51±0.20(Predicted) | [Appearance]
White to off-white Solid | [CAS DataBase Reference]
20870-90-0 |
| Hazard Information | Back Directory | [Uses]
5-Bromo-1-methyl-2-oxoindoline is a useful intermediate for organic synthesis. It is used as an intermediate in the preparation of symmetric cyclic indole-tetramers and some substituted oxindoles. | [Synthesis]
General procedure for the synthesis of 5-bromo-1-methyl-2-oxodihydroindole from 1-methyl-2-indolinone: N-methylindole (0.5 g, 3.4 mmol) was dissolved in acetonitrile (5 mL) and stirred at 0 °C. Subsequently, N-bromosuccinimide (NBS, 0.62 g) dissolved in acetonitrile (10 mL) was added slowly and dropwise. The reaction mixture was kept stirred at 0 °C for 1 h, followed by continued stirring for 2 h at room temperature. After completion of the reaction, the solvent was removed by rotary evaporation and the resulting solid was dissolved in chloroform (CHCl3) and washed twice with deionized water. After removing the chloroform again by rotary evaporation, the resulting brown solid was recrystallized with hexane to give 5-bromo-N-methylhydroxyindole (0.44 g, 58% yield). The product was characterized by 1H-NMR (300 MHz, CDCl3) with the following chemical shifts δ (ppm): 7.42-7.39 (d, 1H), 7.26 (s, 1H), 6.71-6.68 (d, 1H), 3.52-3.20 (s, 2H), 3.19 (s, 3H). | [References]
[1] European Journal of Organic Chemistry, 2011, # 20-21, p. 3781 - 3793
[2] RSC Advances, 2016, vol. 6, # 74, p. 70221 - 70225
[3] Molecular Crystals and Liquid Crystals, 2015, vol. 618, # 1, p. 47 - 54
[4] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>128, p. 1,23 |
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